CN108822019B - Polar fluorescence probe of a kind of detection fat drips and its preparation method and application - Google Patents
Polar fluorescence probe of a kind of detection fat drips and its preparation method and application Download PDFInfo
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Abstract
The present invention provides a kind of polar fluorescence probe of detection fat drips, chemical name 3-(4-(2,2- dicyanoethenyls) phenyl) -9- ethyl carbazole, structural formula is；Since there are intramoleculars to distort electronics transfer effect (TICT) for the probe, to realize the good response to solvent polarity.Fluorescence probe of the invention generally electroneutral, can be such that it is positioned in fat drips in the cell well.The probe can accurately be positioned at fat drips, sensitivity with higher, good optical stability and to polarity specificly-response；And it realizes to the polar detection of intracellular fat drips.The synthetic method of the probe, step is simple, purifying is convenient, high income.
Description
Technical field
The invention belongs to small organic molecule fluorescence probe fields, and in particular to a kind of polar fluorescence probe of detection fat drips and
Preparation method and application.
Background technique
Cancer is generally acknowledged one of the incurable disease in the whole world, has a large amount of people to die of cancer every year.Although cancer is important
Disease, but if our timely Clinics and Practices, cancer mortality be can control.It is examined at present by tumor markers
Disconnected cancer has become hot spot, although existing some tumor markers have substantially increased cancer diagnosis rate, due to
They have the shortcomings that invasive and inconvenient for operation and limit their extensive use.Therefore, develop new tumour mark
Note object has a very important significance the Clinics and Practices of cancer.In recent years, fat drips because its unique structure and performance it is extensive
Ground causes everybody concern.Fat drips are also related with many important physiological activities other than providing energy for cell.Have
According to the report, the metabolic mechanism due to fat drips is different, so polarity of the fat drips in cancer cell can be bigger than in normal cell.
Therefore, the polarity of fat drips can be used as an important indicator for distinguishing cancer cell and normal cell.So detecting the polarity of fat drips
Important tutorial message will be provided for the diagnosis of cancer.
Currently, Imaging-PAM is since it is highly sensitive, Non-invasive detection and highly selective, it has also become detect biological micropolar
The powerful of property environment.Therefore, develop diagnosis of the polarity for cancer that the new polarity probes of one kind detect intracellular fat drips
Have great importance with clinical research.
Summary of the invention
Aiming at the problems existing in the prior art, the present invention, which provides, a kind of can detect polar fluorescence probe in fat drips.It should
Probe has hypotoxicity, and fat drips can be accurately positioned and to polarity specificly-response in good optical stability.
It is a further object of the present invention to provide a kind of synthetic method of above-mentioned fluorescence probe, raw material is easy to get, synthesis step is simple
Single, high income.
To achieve the above object, the present invention adopts the following technical scheme that.
A kind of intracellular polar fluorescence probe of fat drips of detection, chemical name 3-(4-(2,2- dicyanoethenyl) benzene
Base) -9- ethyl carbazole, referred to as EBMC, structural formula such as formula (I):
Formula (I).
A kind of synthetic method of above-mentioned fluorescence probe, comprising the following steps:
(1) sodium hydroxide solution of 3- bromine carbazole (1) is stirred at room temperature in tetrahydrofuran, then heats with bromoethane (2)
Reaction, isolates and purifies to obtain white solid, i.e. the bromo- 9- ethyl carbazole (3) of 3-:
；
(2) the bromo- 9- ethyl carbazole (3) of 3- and 4- formylphenylboronic acid (4) exist in potassium carbonate and tetrakis triphenylphosphine palladium
Under be heated to reflux in the in the mixed solvent of tetrahydrofuran and water, isolate and purify to obtain 3-(4- carboxaldehyde radicals phenyl) -9- ethyl carbazole
(5):
；
(3) 3-(4- carboxaldehyde radicals phenyl) -9- ethyl carbazole (5) and malononitrile (6) in the presence of piperidines in organic solvent
It is heated to reflux, isolates and purifies to obtain 3-(4-(2,2- dicyanoethenyl) phenyl) -9- ethyl carbazole (7), i.e. fluorescence probe
EBMC:
。
In step (1), the 3- bromine carbazole: sodium hydroxide: the molar ratio of bromoethane is 1:2:6.
In step (1), the mixing time is 1.5h；The reaction temperature is 55 DEG C, reaction time 12h.
In step (1), the purification procedures are as follows: the system after reaction is evaporated under reduced pressure, solvent is spin-dried for and is slightly produced
After object, purified product is obtained through pillar layer separation；The mobile phase of the pillar layer separation is preferably the acetic acid that volume ratio is 1:30
Ethyl ester and petroleum ether.
In step (2), the bromo- 9- ethyl carbazole of 3-: potassium carbonate: 4- formylphenylboronic acid: tetrakis triphenylphosphine palladium
Molar ratio is 1:3:1.2:0.03.
In step (2), the reaction temperature is 60 DEG C, reaction time 12h.
In step (2), the reaction is in N2Protection is lower to be carried out.
In step (2), the tetrahydrofuran: water=1:3(V:V).
In step (2), the purification procedures are as follows: the body after reaction is extracted with dichloromethane in the system after reaction
System, and with a small amount of water remaining in anhydrous sodium sulfate removing system, it is then evaporated under reduced pressure, is spin-dried for solvent and obtains crude product,
Purified product is obtained through pillar layer separation；The mobile phase of the pillar layer separation be preferably volume ratio be 1:20 ethyl acetate with
Petroleum ether.
In step (3), the 3-(4- carboxaldehyde radicals phenyl) molar ratio of -9- ethyl carbazole and malononitrile is 1:3.
In step (3), the reaction temperature is 80 DEG C, reaction time 12h.
In step (3), the reaction dissolvent is preferably the mixed liquor of ethyl alcohol and acetonitrile；The volume ratio of ethyl alcohol and acetonitrile is preferred
For 1:1.
Separating-purifying step described in step (3) are as follows: the system after reaction is evaporated under reduced pressure, solvent is spin-dried for and obtains crude product
Afterwards, purified product is obtained through pillar layer separation；The mobile phase of the pillar layer separation is preferably the acetic acid second that volume ratio is 1:20
Ester and petroleum ether.
A kind of above-mentioned fluorescence probe is for detecting solution and the polar application of intracellular fat drips.
The recognition mechanism of fluorescence probe of the present invention is as follows:
Since malononitrile is a strong electron-withdrawing group group, 9- ethyl carbazole is an electron-donating group, so in probe
In EBMC structure, there is the electronics transfer partially occurred from " carbazole " to " malononitrile " part, i.e. cyclic voltammetry method (ICT)
Effect.Exactly this ICT effect makes probe have " solvation effect ".(the tetrahydrofuran solvent pole within the scope of certain polarity
Before property), since " negative solvent effect " accounts for main function so that probe with the polar increase fluorescence intensity of polar solvent gradually
Increase；As solvent polarity further increases (after tetrahydrofuran solvent polarity), since " positive solvent effect " accounts for leading role,
So that fluorescence probe intensity reduces with polar variation.However, no matter in normal cell or in cancer cell, fat drips
Polarity all can before tetrahydrofuran polarity, also, in cancer cell fat drips polarity can be less than normal cell in fat drips pole
Property.So when probe can issue weaker fluorescence in the lesser cancer cell fat drips environment of polarity, and it is biggish normal in polarity
Cytolipin drip ring can issue stronger fluorescence in border.Therefore, normal cell and cancer cell can by the variation of fluorescence intensity into
Row is distinguished, to realize the diagnosis of diagnosis cancer.
The invention has the benefit that
It is provided by the present invention to distinguish the different polar fluorescence probes of fat drips, fat drips can accurately be positioned at, are had higher
Sensitivity, good optical stability and to polarity specificly-response；And it realizes to the polar inspection of intracellular fat drips
It surveys.Meanwhile the present invention provides the synthetic methods of the probe, step is simple, purifying is convenient, high income.
Detailed description of the invention
Fig. 1 is probe1H H NMR spectroscopy；
Fig. 2 is probe13C H NMR spectroscopy；
Fig. 3 is emission spectrum of the probe in opposed polarity solvent；
Fig. 4 is the common location of probe and commercialization fat drips dyestuff；
Fig. 5 is imaging applications of the probe in different cells.
Specific embodiment
Below with reference to embodiment and attached drawing, the present invention will be further described, but the present invention is not by the limit of following embodiments
System.
The synthesis of 1 fluorescence probe EBMC of embodiment
(1) synthesis of compound (3)
2.46 g 3- bromine carbazoles (10 mmol) (1) and 0.8 g sodium hydroxide (20 mmol) are added, 20 mL tetra- are housed
It in the high-voltage tube of hydrogen furans, is stirred at room temperature, 6.56 g bromoethanes (60mmol) is added after 1.5h, react about 12h, reaction is completed
Afterwards, the system after reaction is evaporated under reduced pressure, is spin-dried for after solvent obtains crude product, is the ethyl acetate and petroleum of 1:30 with volume ratio
Ether is that mobile phase progress pillar layer separation purifies to obtain the bromo- 9- ethyl carbazole (3) of 3-；
(2) synthesis of compound (5):
Weigh the bromo- 9- ethyl carbazole (3) (1 mmol) of 0.274 g3-, 0.18 g4- formylphenylboronic acid (4) (1.2
Mmol), 37 tetra--(triphenylphosphine palladiums) of mg (0.03 mmol), 0.445g potassium carbonate (3.23 mmol) are in tetrahydrofuran: water=1:
In the mixed solvent hybrid reaction 3(V:V) is warming up to 60 DEG C of reflux, in N2After reacting 12 h under atmosphere environment, dichloromethane is used
It after alkane extraction, and with a small amount of water remaining in anhydrous sodium sulfate removing system, is then evaporated under reduced pressure, is spin-dried for solvent and obtains slightly to produce
Product, ethyl acetate and petroleum ether using volume ratio for 1:20 carry out pillar layer separation as mobile phase and purify to obtain 3-(4- carboxaldehyde radicals benzene
Base) -9- ethyl carbazole (5).
(3) synthesis of compound (7):
Weigh 0.299 g3-(4- carboxaldehyde radicals phenyl) -9- ethyl carbazole (5) (1 mmol) and 0.193 g malononitrile (3
Mmol) in ethyl alcohol: acetonitrile=1:1(V:V) mixed liquor in, three drop piperidines are added dropwise, are warming up to 80 DEG C of reflux, after 12 h of reaction,
Vacuum distillation is spin-dried for after solvent obtains crude product, with mobile phase volume than the ethyl acetate and petroleum ether pillar layer separation for 1:20
Obtain the pure products probe EBMC of orange.
Probe1H H NMR spectroscopy such as Fig. 1,13C H NMR spectroscopy such as Fig. 2；
1H NMR (400 MHz, DMSO-d 6) δ 8.69 (d, J = 2.0 Hz, 1H), 8.52 (s, 1H),
8.27 (d, J = 7.6 Hz, 1H), 8.08 (6.8 Hz, 4H), 7.92 (dd, J1 = 8.6, J2 = 1.8 Hz,
1H), 7.71 (d, J = 8.4 Hz, 1H), 7.64 (d, J = 8.4 Hz, 1H), 7.49 (m, 1H), 7.25
(t, J = 7.4 Hz, 1H), 4.47 (q, J = 7.2 Hz, 2H), 1.33 (t, J = 7.0 Hz, 3H)；
13C NMR (100 MHz, DMSO-d6) δ 160.91, 147.04, 140.30, 140.19, 131.65,
129.45, 128.99, 127.28, 126.41, 125.10, 123.18, 122.55, 120.91, 119.49,
119.42 , 114.79, 109.99, 109.64, 79.62, 37.33, 13.93。
Emission spectrum of 2 fluorescence probe of embodiment in different solvents
Compound concentration is that the test mother liquor of the dimethyl sulfoxide (DMSO) of 1 mM embodiment, 1 gained fluorescence probe EBMC waits for
With.
In test fluid, the solvent of 3 mL opposed polarities: toluene (Toluene) is taken respectively, dioxane (Dioxane), four
Hydrogen furans (THF), methylene chloride (DCM), acetone (Acetone), dimethyl sulfoxide (DMSO), it is 1mM's that concentration, which is then added,
Then probe mother liquor carries out fluorescent scanning (excitation wavelength 455nm, inspection so that the ultimate density of test fluid middle probe is 10 μM
Survey wave band 450-800nm), fluorescence intensity in each system is obtained, as shown in Figure 3.From the figure 3, it may be seen that with the increase of solvent polarity, light
Red shift is composed, before tetrahydrofuran solution, fluorescence intensity increases with polar increase；After tetrahydrofuran, fluorescence is strong
Degree weakens with polar increase.
The common location of 3 fluorescence probe of embodiment and commercialization fat drips dyestuff
Compound concentration is that the test mother liquor of the dimethyl sulfoxide (DMSO) of 1 mM embodiment, 1 gained fluorescence probe EBMC waits for
With；Compound concentration is the test mother liquor of the dimethyl sulfoxide (DMSO) of the commercially available Nile red (the dedicated targeting agents of fat drips) of 1mM
For use.
The mouse mammary tumor cells 4T1 of suitable density is inoculated into the 35 mm imaging culture dish of sterilizing, in CO2Training
Supporting case, (temperature is 37 DEG C, 5 % CO2) in culture, after cell is adherent, while fluorescence probe EBMC and fat drips into cell
It is commercialized dyestuff Nile red, makes 10 μM of fluorescence probe ultimate density, Nile red ultimate density is 5 μM.After half an hour, training is discarded
Base is supported, is rinsed cell 3 times with PBS buffer solution, then carries out fluorescence imaging (excitation wavelength: 488 nm, green channel 500-550
nm；Excitation wavelength: 561nm, red channel 570nm-620nm), imaging results are as shown in Figure 4.Wherein, (A) is EBMC in green
The image in channel；It (B) is image of the Nile red in red channel；It (C) is the stacking chart of (A) and (B)；(D) for (A) and
(B) spectral intensity stacking chart；(E) the intensity scatter plot in two channels；It (F) is cell light field image.As shown in Figure 4, should
The imaging position of probe and Nile red is identical, and illustrates that probe EBMC is primarily located in the fat drips in cell, thus this hair
Bright probe can be used to detect the polarity of fat drips in cell.
The cell imaging of 4 fluorescence probe of embodiment
Compound concentration is that the test mother liquor of the dimethyl sulfoxide (DMSO) of 1 mM embodiment, 1 gained fluorescence probe EBMC waits for
With.
The normal cell 3T3 of suitable density and cancer cell 4T1 are inoculated into the 35 mm imaging culture of two sterilizings respectively
In ware, in CO2(temperature is 37 DEG C to incubator, 5 % CO2) in culture, after cell is adherent, be added fluorescence probe EBMC, make to visit
The ultimate density of needle is 10 μM, discards culture medium, is rinsed cell 3 times with PBS buffer solution, then carries out fluorescence imaging (excitation
Wavelength: 488 nm；Emission band: 500-550 nm), fluorescence imaging result is as shown in Figure 5.As shown in Figure 5, in normal cell
Fluorescence obviously than the light intensity in tumour cell, so, tumour cell and normal cell can pass through the variation of fluorescence probe intensity
It distinguishes.Therefore, fluorescence probe EBMC of the invention can diagnose cancer by detecting the polarity of fat drips.
Claims (10)
1. a kind of polar fluorescence probe of detection fat drips, chemical name 3-(4-(2,2- dicyanoethenyl) phenyl) -9- second
Base carbazole, structural formula such as formula (I):
Formula (I).
2. a kind of synthetic method of fluorescence probe as described in claim 1, which comprises the following steps:
(1) sodium hydroxide solution of 3- bromine carbazole (1) is stirred at room temperature in tetrahydrofuran, then reacts with bromoethane (2) heating, point
White solid is obtained from purifying, i.e. the bromo- 9- ethyl carbazole (3) of 3-:
；
(2) the bromo- 9- ethyl carbazole (3) of 3- and 4- formylphenylboronic acid (4) in the presence of potassium carbonate and tetrakis triphenylphosphine palladium in
The mixed solvent of tetrahydrofuran and water is heated to reflux, and isolates and purifies to obtain 3-(4- carboxaldehyde radicals phenyl) -9- ethyl carbazole (5):
；
(3) 3-(4- carboxaldehyde radicals phenyl) -9- ethyl carbazole (5) and malononitrile (6) heat in organic solvent in the presence of piperidines
Reflux, isolates and purifies to obtain 3-(4-(2,2- dicyanoethenyl) phenyl) -9- ethyl carbazole (7):
。
3. synthetic method according to claim 2, which is characterized in that 3- bromine carbazole described in step (1): sodium hydroxide:
The molar ratio of bromoethane is 1:2:6；The bromo- 9- ethyl carbazole of 3- described in step (2): potassium carbonate: 4- formylphenylboronic acid: four
The molar ratio of (triphenylphosphine) palladium is 1:3:1.2:0.03；In step (3), the 3-(4- carboxaldehyde radicals phenyl) -9- ethyl carbazole
Molar ratio with malononitrile is 1:3.
4. synthetic method according to claim 2, which is characterized in that mixing time described in step (1) is 1.5h；It is described
Reaction temperature is 55 DEG C, reaction time 12h；Reaction temperature described in step (2) is 60 DEG C, reaction time 12h；Step
(3) reaction temperature described in is 80 DEG C, reaction time 12h.
5. synthetic method according to claim 2, which is characterized in that mixed solvent tetrahydrofuran described in step (2): water
=1:3(V:V)；Reaction dissolvent described in step (3) is ethyl alcohol: acetonitrile=1:1(V:V).
6. synthetic method according to claim 2, which is characterized in that reaction is in N described in step (2)2Protection is lower to be carried out.
7. synthetic method according to claim 2, which is characterized in that purification procedures described in step (1) are as follows: will be anti-
System vacuum distillation after answering is spin-dried for after solvent obtains crude product, obtains purified product through pillar layer separation；The column chromatography point
From mobile phase be preferably volume ratio be 1:30 ethyl acetate and petroleum ether.
8. synthetic method according to claim 2, which is characterized in that purification procedures described in step (2) are as follows: will be anti-
The system after reaction is extracted with dichloromethane in system after reaction by the system after answering, and is remained in anhydrous sodium sulfate removing system
Remaining a small amount of water, is then evaporated under reduced pressure, and is spin-dried for solvent and is obtained crude product, obtains purified product through pillar layer separation；It is described
The mobile phase of pillar layer separation is preferably the ethyl acetate and petroleum ether that volume ratio is 1:20.
9. synthetic method according to claim 2, which is characterized in that separating-purifying step described in step (3) are as follows: will be anti-
System vacuum distillation after answering is spin-dried for after solvent obtains crude product, obtains purified product through pillar layer separation；The column chromatography point
From mobile phase be preferably volume ratio be 1:20 ethyl acetate and petroleum ether.
10. a kind of fluorescence probe as described in claim 1 is used to prepare detection solution and intracellular fat drips polar reagent is answered
With.
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